CA2860834A1 - Process for making hmf and hmf derivatives from sugars, with recovery of unreacted sugars suitable for direct fermentation to ethanol - Google Patents
Process for making hmf and hmf derivatives from sugars, with recovery of unreacted sugars suitable for direct fermentation to ethanol Download PDFInfo
- Publication number
- CA2860834A1 CA2860834A1 CA2860834A CA2860834A CA2860834A1 CA 2860834 A1 CA2860834 A1 CA 2860834A1 CA 2860834 A CA2860834 A CA 2860834A CA 2860834 A CA2860834 A CA 2860834A CA 2860834 A1 CA2860834 A1 CA 2860834A1
- Authority
- CA
- Canada
- Prior art keywords
- hmf
- sugars
- product
- percent
- process according
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Abandoned
Links
- 235000000346 sugar Nutrition 0.000 title claims abstract description 151
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 title claims abstract description 110
- 150000008163 sugars Chemical class 0.000 title claims abstract description 93
- 238000000855 fermentation Methods 0.000 title claims abstract description 26
- 230000004151 fermentation Effects 0.000 title claims abstract description 26
- 238000000034 method Methods 0.000 title claims description 61
- 230000008569 process Effects 0.000 title claims description 43
- 238000011084 recovery Methods 0.000 title abstract description 12
- NOEGNKMFWQHSLB-UHFFFAOYSA-N 5-hydroxymethylfurfural Chemical compound OCC1=CC=C(C=O)O1 NOEGNKMFWQHSLB-UHFFFAOYSA-N 0.000 claims abstract description 150
- RJGBSYZFOCAGQY-UHFFFAOYSA-N hydroxymethylfurfural Natural products COC1=CC=C(C=O)O1 RJGBSYZFOCAGQY-UHFFFAOYSA-N 0.000 claims abstract description 145
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- 238000006243 chemical reaction Methods 0.000 claims abstract description 48
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- 238000006297 dehydration reaction Methods 0.000 claims abstract description 35
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- 239000000243 solution Substances 0.000 claims description 58
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims description 36
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- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 claims description 26
- 239000008103 glucose Substances 0.000 claims description 26
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- WQZGKKKJIJFFOK-VFUOTHLCSA-N beta-D-glucose Chemical compound OC[C@H]1O[C@@H](O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-VFUOTHLCSA-N 0.000 claims description 12
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- 239000003960 organic solvent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920003053 polystyrene-divinylbenzene Polymers 0.000 description 1
- 239000011814 protection agent Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 230000008929 regeneration Effects 0.000 description 1
- 238000011069 regeneration method Methods 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 208000007056 sickle cell anemia Diseases 0.000 description 1
- 238000007086 side reaction Methods 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 239000011949 solid catalyst Substances 0.000 description 1
- 239000002910 solid waste Substances 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 238000007738 vacuum evaporation Methods 0.000 description 1
- 238000003828 vacuum filtration Methods 0.000 description 1
- 230000035899 viability Effects 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C29/00—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring
- C07C29/132—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group
- C07C29/136—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH
- C07C29/14—Preparation of compounds having hydroxy or O-metal groups bound to a carbon atom not belonging to a six-membered aromatic ring by reduction of an oxygen containing functional group of >C=O containing groups, e.g. —COOH of a —CHO group
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/38—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D307/40—Radicals substituted by oxygen atoms
- C07D307/46—Doubly bound oxygen atoms, or two oxygen atoms singly bound to the same carbon atom
- C07D307/48—Furfural
- C07D307/50—Preparation from natural products
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P13/00—Preparation of nitrogen-containing organic compounds
- C12P13/04—Alpha- or beta- amino acids
- C12P13/08—Lysine; Diaminopimelic acid; Threonine; Valine
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
- C12P7/06—Ethanol, i.e. non-beverage
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/02—Preparation of oxygen-containing organic compounds containing a hydroxy group
- C12P7/04—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic
- C12P7/18—Preparation of oxygen-containing organic compounds containing a hydroxy group acyclic polyhydric
-
- C—CHEMISTRY; METALLURGY
- C12—BIOCHEMISTRY; BEER; SPIRITS; WINE; VINEGAR; MICROBIOLOGY; ENZYMOLOGY; MUTATION OR GENETIC ENGINEERING
- C12P—FERMENTATION OR ENZYME-USING PROCESSES TO SYNTHESISE A DESIRED CHEMICAL COMPOUND OR COMPOSITION OR TO SEPARATE OPTICAL ISOMERS FROM A RACEMIC MIXTURE
- C12P7/00—Preparation of oxygen-containing organic compounds
- C12P7/40—Preparation of oxygen-containing organic compounds containing a carboxyl group including Peroxycarboxylic acids
- C12P7/56—Lactic acid
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E50/00—Technologies for the production of fuel of non-fossil origin
- Y02E50/10—Biofuels, e.g. bio-diesel
Landscapes
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Life Sciences & Earth Sciences (AREA)
- Zoology (AREA)
- Wood Science & Technology (AREA)
- Health & Medical Sciences (AREA)
- General Engineering & Computer Science (AREA)
- General Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Biotechnology (AREA)
- Biochemistry (AREA)
- Bioinformatics & Cheminformatics (AREA)
- Microbiology (AREA)
- General Health & Medical Sciences (AREA)
- Genetics & Genomics (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
- Saccharide Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US201261584900P | 2012-01-10 | 2012-01-10 | |
| US61/584,900 | 2012-01-10 | ||
| PCT/US2012/066708 WO2013106136A1 (en) | 2012-01-10 | 2012-11-28 | Process for making hmf and hmf derivatives from sugars, with recovery of unreacted sugars suitable for direct fermentation to ethanol |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2860834A1 true CA2860834A1 (en) | 2013-07-18 |
Family
ID=48781802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA2860834A Abandoned CA2860834A1 (en) | 2012-01-10 | 2012-11-28 | Process for making hmf and hmf derivatives from sugars, with recovery of unreacted sugars suitable for direct fermentation to ethanol |
Country Status (13)
Families Citing this family (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US9630974B2 (en) | 2013-03-05 | 2017-04-25 | Archer-Daniels-Midland Co. | Process for acid dehydration of sugar alcohols |
| JP6394221B2 (ja) * | 2013-09-20 | 2018-09-26 | 三菱ケミカル株式会社 | 精製糖液の製造方法、有機化合物の製造方法および微生物の培養方法 |
| JP2017505310A (ja) * | 2014-01-27 | 2017-02-16 | レノビア インコーポレイテッド | Ｈｍｆ含有生成物へのフルクトース含有供給原料の変換 |
| JP6275278B2 (ja) * | 2014-04-10 | 2018-02-07 | アーチャー−ダニエルズ−ミッドランド カンパニー | 酸触媒の組合せ混合物を用いた糖アルコールの脱水 |
| CA2956953C (en) | 2014-08-19 | 2021-06-29 | Archer Daniels Midland Company | Heterogeneous ruthenium-based catalyst and process for producing 2,5-furandicarboxylic acid from hydroxymethylfurfural in water |
| KR101626808B1 (ko) | 2014-10-29 | 2016-06-02 | 군산대학교산학협력단 | 목질계 바이오매스 가수분해액으로부터 당을 정제하는 방법 |
| EP3253486B1 (en) * | 2015-02-03 | 2019-12-25 | Archer Daniels Midland Company | One vessel process for making 1,2-propanediol from a high fructose feedstock |
| BR112017017105A2 (pt) | 2015-02-10 | 2018-04-03 | Avantium Knowledge Centre Bv | composição, e, uso de huminas. |
| ES2965441T3 (es) | 2015-04-14 | 2024-04-15 | Du Pont | Procedimientos para producir ácido 2,5-furandicarboxílico y derivados del mismo |
| WO2017034985A1 (en) * | 2015-08-21 | 2017-03-02 | Gfbiochemicals Limited | Process to prepare hydroxymethylfurfural derivatives |
| AU2017207824B2 (en) | 2016-01-13 | 2021-05-20 | Stora Enso Oyj | Processes for the preparation of 2,5-furandicarboxylic acid and intermediates and derivatives thereof |
| DE102016224073A1 (de) | 2016-12-02 | 2018-06-07 | Südzucker AG | Verbessertes HMF-Herstellungsverfahren |
| EP3424914A1 (de) * | 2017-07-05 | 2019-01-09 | AVALON Industries AG | Verfahren zur extraktion von 5-hydroxymethylfurfural (5-hmf) |
| KR102568266B1 (ko) | 2017-07-12 | 2023-08-17 | 스토라 엔소 오와이제이 | 정제된 2,5-푸란디카르복실산 경로 생성물 |
| DE102018208510A1 (de) | 2018-05-29 | 2019-12-05 | Südzucker AG | Salz- und Säuregemisch-katalysierte HMF-Herstellung |
| DE102018208507A1 (de) * | 2018-05-29 | 2019-12-05 | Südzucker AG | Anolytfraktion-katalysierte HMF-Herstellung |
| US11578347B2 (en) * | 2020-09-01 | 2023-02-14 | Braskem S.A. | Anaerobic fermentative production of furandimethanol and enzymatic production of furandicarboxylic acid |
| US20240059833A1 (en) | 2020-12-18 | 2024-02-22 | Basf Se | Polyester polyols comprising 2,5-bis(hydroxymethyl)tetrahydrofuran |
Family Cites Families (18)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB600871A (en) * | 1945-10-17 | 1948-04-21 | Walter Norman Haworth | Improvements relating to the manufacture of 5-hydroxymethyl 2-furfural |
| US2929823A (en) * | 1956-11-26 | 1960-03-22 | Merck & Co Inc | Production of 5-hydroxymethylfurfural |
| CA1173381A (en) * | 1980-03-05 | 1984-08-28 | Peter L. Rogers | Ethanol production in a continuous process with cell recycle |
| DE3601281A1 (de) * | 1986-01-17 | 1987-07-23 | Sueddeutsche Zucker Ag | Verfahren zur herstellung von 5-hydroxymethylfurfural einschliesslich eines kristallinen produktes unter ausschliesslicher verwendung von wasser als loesungsmittel |
| FR2664273B1 (fr) * | 1990-06-27 | 1994-04-29 | Beghin Say Sa | Nouveau procede de preparation du 5-hydroxymethylfurfural a partir de saccharides. |
| AU4700199A (en) * | 1998-06-23 | 2000-01-10 | Regents Of The University Of California, The | Method of treating biomass material |
| EP1834950A1 (en) * | 2006-03-10 | 2007-09-19 | Avantium International B.V. | Method for the synthesis of 5-alkoxymethylfurfural ethers and their use |
| EP1834951A1 (en) * | 2006-03-10 | 2007-09-19 | Avantium International B.V. | Method for the synthesis of organic acid esters of 5-hydroxymethylfurfural and their use |
| EP2183236B1 (en) * | 2007-09-07 | 2011-02-16 | Furanix Technologies B.V. | Hydroxymethylfurfural ethers and esters prepared in ionic liquids |
| HUE032843T2 (en) * | 2007-12-12 | 2017-11-28 | Archer-Daniels-Midland Company | Conversion of carbohydrates to hydroxymethyl furfural (HMF) and its derivatives |
| WO2010055189A1 (es) * | 2008-11-17 | 2010-05-20 | Ingelia, S.L. | Sistema de control de presión y temperatura de al menos un reactor químico |
| CN101475543A (zh) * | 2009-02-11 | 2009-07-08 | 中国科学院山西煤炭化学研究所 | 一种由糖类低温常压制取羟甲基糠醛的方法 |
| FR2945543B1 (fr) * | 2009-05-15 | 2011-05-06 | Inst Francais Du Petrole | Procede de production d'alcools et/ou de solvants a partir de biomasse lignocellulosique avec recyclage acide des residus solides |
| US20100311137A1 (en) * | 2009-06-08 | 2010-12-09 | Ut-Battelle, Llc | Microorganisms Having Enhanced Tolerance To Inhibitors and Stress |
| JP2011078327A (ja) * | 2009-10-05 | 2011-04-21 | Gunma Univ | 糖溶液からの発酵阻害物質の分離方法 |
| WO2011133536A1 (en) * | 2010-04-19 | 2011-10-27 | The University Of Toledo | Aldose-ketose transformation for separation and/or chemical conversion of c6 and c5 sugars from biomass materials |
| CN102260229A (zh) * | 2010-05-28 | 2011-11-30 | 中国科学院大连化学物理研究所 | 一种制备5-羟甲基糠醛及5-烷氧基甲基糠醛的方法 |
| EP2825543B1 (en) * | 2012-03-12 | 2017-12-20 | Archer Daniels Midland Company | Process for making sugar and/or sugar alcohol dehydration products |
-
2012
- 2012-11-28 EA EA201491190A patent/EA201491190A1/ru unknown
- 2012-11-28 IN IN6491DEN2014 patent/IN2014DN06491A/en unknown
- 2012-11-28 WO PCT/US2012/066708 patent/WO2013106136A1/en active Application Filing
- 2012-11-28 EP EP12864693.2A patent/EP2802570A4/en not_active Withdrawn
- 2012-11-28 MX MX2014008376A patent/MX2014008376A/es unknown
- 2012-11-28 KR KR1020147022308A patent/KR20140117522A/ko not_active Withdrawn
- 2012-11-28 CA CA2860834A patent/CA2860834A1/en not_active Abandoned
- 2012-11-28 AU AU2012364787A patent/AU2012364787A1/en not_active Abandoned
- 2012-11-28 US US14/358,363 patent/US20140315262A1/en not_active Abandoned
- 2012-11-28 BR BR112014016687A patent/BR112014016687A8/pt not_active Application Discontinuation
- 2012-11-28 SG SG11201403204TA patent/SG11201403204TA/en unknown
- 2012-11-28 JP JP2014551244A patent/JP2015504069A/ja active Pending
- 2012-11-28 CN CN201280066380.8A patent/CN104053649A/zh active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| CN104053649A (zh) | 2014-09-17 |
| BR112014016687A8 (pt) | 2017-07-04 |
| EP2802570A1 (en) | 2014-11-19 |
| EP2802570A4 (en) | 2016-01-06 |
| SG11201403204TA (en) | 2014-09-26 |
| JP2015504069A (ja) | 2015-02-05 |
| KR20140117522A (ko) | 2014-10-07 |
| BR112014016687A2 (pt) | 2017-06-13 |
| MX2014008376A (es) | 2015-04-09 |
| WO2013106136A1 (en) | 2013-07-18 |
| AU2012364787A1 (en) | 2014-07-03 |
| US20140315262A1 (en) | 2014-10-23 |
| IN2014DN06491A (enrdf_load_stackoverflow) | 2015-06-12 |
| EA201491190A1 (ru) | 2014-12-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FZDE | Discontinued |
Effective date: 20181128 |